3 years ago

Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (−)-Agroclavine and (−)-Elymoclavine

Regioselective Direct C-4 Functionalization of Indole: Total Syntheses of (−)-Agroclavine and (−)-Elymoclavine
Kuo Yuan, Bin Wang, Yanxing Jia, Yuan Wang, Jianbo Lv
An efficient rhodium-catalyzed method for direct C–H functionalization at the C4 position of unprotected indoles has been developed. The utility of this method is demonstrated by the concise total syntheses of agroclavine and elymoclavine in a divergent manner. These syntheses feature a Pd-catalyzed asymmetric allylic alkylation reaction to assemble the triyclic indole moiety, and a ring-closing metathesis reaction to form the D ring.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01681

DOI: 10.1021/acs.orglett.7b01681

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